Catalytic asymmetric ring opening of meso-epoxides with aromatic amines in water

被引：155

作者：

Azoulay, S ^{[1
]}

Manabe, K ^{[1
]}

Kobayashi, S ^{[1
]}

机构：

[1] Univ Tokyo, HFRE Div, ERATO, Grad Sch Pharmaceut Sci,JST,Bunkyo Ku, Tokyo 1130033, Japan

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 21期

关键词：

D O I：

10.1021/ol051546z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An operationally simple and environmentally benign protocol for the catalytic asymmetric ring opening of meso-epoxides with aromatic amines has been developed. The reactions proceeded smoothly in the presence of 1 mol % Of Sc(OSO3C12H25)(3) and 1.2 mol % of a chiral bipyridine ligand in water to afford beta-amino alcohols in high yields with excellent enantioselectivities.

引用

页码：4593 / 4595

页数：3

共 27 条

[1] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis
Ager, DJ
Prakash, I
Schaad, DR
[J]. CHEMICAL REVIEWS, 1996, 96 (02) : 835 - 875
[2] The synthesis of vicinal amino alcohols
Bergmeier, SC
[J]. TETRAHEDRON, 2000, 56 (17) : 2561 - 2576
[3] SYNTHESIS OF A NOVEL OPTICALLY-ACTIVE C-2-SYMMETRICAL 2,2'-BIPYRIDINE
BOLM, C
EWALD, M
ZEHNDER, M
NEUBURGER, MA
[J]. CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (02): : 453 - 458
[4] Enantioselective ring opening of meso-epoxides by aromatic amines catalyzed by lanthanide iodo binaphtholates
Carrée, F
Gil, R
Collin, J
[J]. ORGANIC LETTERS, 2005, 7 (06) : 1023 - 1026
[5] Cornils B., 2004, Aqueous-Phase Organometallic Catalysis: Concepts and Applications
[6] Efficient ring-opening reaction of epoxides and aziridines promoted by tributylphosphine in water
Fan, RH
Hou, XL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) : 726 - 730
[7] Grieco P.A., 1998, Organic synthesis in water
[8] Enantio- and diastereoselective, stereospecific Mannich-type reactions in water
Hamada, T
Manabe, K
Kodayashi, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (25) : 7768 - 7769
[9] Desymmetric ring-opening of meso-epoxides with anilines:: a simple way to chiral β-amino alcohols
Hou, XL
Wu, J
Dai, LX
Xia, LJ
Tang, MH
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (10) : 1747 - 1752
[10] Micellar media for the efficient ring opening of epoxides with CN-, N3-, NO3-,NO2-, SCN-, Cl- and Br- catalyzed with Ce(OTf)4
Iranpoor, N
Firouzabadi, H
Shekarize, M
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (04) : 724 - 727

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